2,4-Dihydroxybenzaldehyde → 4-Benzyloxy-2-hydroxybenzaldehyde

HRID 1450002Notes

Reaction equation

HRID 1450002 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[F-].[K+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C>[CH2:13]([O:10][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([OH:1])[CH:9]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 72132,4-DihydroxybenzaldehydeHCID 7503Benzyl ChlorideHCID 522689Potassium Fluoride

Product 1

HCID 5612354-Benzyloxy-2-hydroxybenzaldehydeYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To solution of 2,4-dihydroxybenzaldehyde (160 g, 1.16 moles) in acetonitrile (2 L) was added potassium fluoride (134 g, 2.30 moles) and benzyl chloride (257 g, 2.03 moles). The reaction was heated to reflux and the volume of solvent was reduced by distillation to approximately half of original over the period of 24 hours. When less than 8% of starting material remains as observed by HPLC the residual acetonitrile is evaporated at reduced pressure and the residue was suspended in water. The aqueous mixture was extracted with ethyl acetate several times and the combined extracts were washed with potassium carbonate, hydrochloric acid and brine. Evaporation of the organic solvent at reduced pressure afforded the crude product in 76% yield. If needed, the product may be recrystallized from t-butyl methyl ether and hexane.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. distillationthe volume of solvent was reduced by distillation to approximately half of original over the period of 24 hours
  4. customis evaporated at reduced pressure
  5. extractionThe aqueous mixture was extracted with ethyl acetate several times
  6. washthe combined extracts were washed with potassium carbonate, hydrochloric acid and brine
  7. customEvaporation of the organic solvent at reduced pressure

Sources & evidence

ORD record
ord-e005f0a3c2f24802a23b7f6db3bb483c
Source dataset
uspto-grants-1997_02
Patent number
US05599988

Reaction notes

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